反-4-羧基-5-辛基-3-甲基-丁内酯

中文名称:

反-4-羧基-5-辛基-3-甲基-丁内酯

中文同义词:

反式-四氢-4-亚甲基-2-辛基-5-氧代-3-呋喃羧酸;反-4-羧基-5-辛基-3-甲基-丁内酯;脂肪酸合成酶FASN有效抑制剂(C75 TRANS);C75反式

英文名称:

C75

英文同义词:

TETRAHYDRO-4-METHYLENE-2-OCTYL-5-OXO-3-FURANCARBOXYLIC ACID;C75;(2S,3R)-4-methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid;(2R,3S)-4-METHYLIDENE-5-OXO-2-N-OCTYL-OXOLANE-3-CARBOXYLIC ACID;(2R*,3S*)-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylicacid;(2R,3S)-rel-Tetrahydro-4-Methylene-2-octyl-5-oxo-3-furancarboxylic Acid;trans-Tetrahydro-4-Methylene-2-octyl-5-oxo-3-furancarboxylic Acid;trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

CAS号:

191282-48-1

分子式:

C14H22O4

分子量:

254.32

EINECS号:

相关类别:

细胞生物学试剂;抑制剂;pharmacetical

Mol文件:

191282-48-1.mol

沸点 

432.1±45.0 °C(Predicted)

密度 

1.08±0.1 g/cm3(Predicted)

储存条件 

2-8°C

溶解度 

DMSO: 18 mg/mL

形态

solid

酸度系数(pKa)

3.08±0.40(Predicted)

颜色

off-white

生物活性

C75 trans (trans-C75, (±)-C75) 是一种 fatty acid synthase (FAS/FASN) 的新型有效的合成抑制剂，在成株试验和球体生长测定中的IC50值分别为35 μM和50 μM。C75 可用作研究代谢紊乱和癌症中脂肪酸合成的工具。

靶点

Target Value FASN (clonogenic assay) 35 μM FASN (spheroid growth assay) 50 μM

Target

Value

FASN (clonogenic assay)

35 μM

FASN (spheroid growth assay)

50 μM

体外研究

trans-C75 ((±)-C75) inhibits PC3 cell growht with an IC 50 of 35 μM at 24 h. trans-C75 ((±)-C75)(10-50 μM) also reduces the growth of LNCaP spheroids in a concentration-dependent manner with an IC 50 of 50 μM. trans-C75 ((±)-C75) inhibits FAS activity and has a cytotoxic effect on tumor cell lines, without affecting food consumption. trans-C75 ((±)-C75) inhibits CPT1 and its administration produces anorexia, suggesting that central inhibition of CPT1 is essential for the anorectic effect of C75. The differential activity of C75 enantiomers may lead to the development of potential new specific drugs for cancer and obesity.

体内研究

C75 blocks fasting-induced c-Fos expression in the arcuate nucleus (Arc), lateral hypothalamic area (LHA), and paraventricular nucleus (PVN) 10–24 h after i.p. injection. Intraperitoneal administration of C75 at 30 mg/kg body weight inhibits food intake of mice by ≥95% within 2 h after i.p. injection. C75-treated DIO mice has a 50% greater weight loss, and a 32.9% increased production of energy because of fatty acid oxidation. C75 treatment of rodent adipocytes and hepatocytes and human breast cancer cells increases fatty acid oxidation and ATP levels by increasing CPT-1 activity, even in the presence of elevated concentrations of malonyl-CoA.

WGK Germany 

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